Between the 1780s and the 1810s, there was only very slow progress toward Maine separating from Massachusetts. The Massachusetts legislature was not completely inattentive during this time, creating new district courts in Maine and allowing the counties in Maine to vote on the issue several times, with each successive occasion garnering a greater portion of the vote. Mainers, both in favor and in opposition to separation, were also active in rallying support during these years, publishing countless newspaper articles and pamphlets on the subject, as well as holding several separation conventions in Portland and Brunswick.
Pro-separation writers tended to emphasize the distinctiveness of Maine and the need for a smaller legislature, composed of men who understood the local environment and economic conditions, and who could effectively legislate on behalf of Mainers. They argued that if smaller states like Vermont and New Hampshire could govern themselves, so too could Maine. That was especially true because Massachusetts, they contended, had a history of vacillating between mismanaging and neglecting Maine, as seen in the War of 1812, when the state government did not send the militia to oust the British from occupied Castine and Eastport.
Anti-separation arguments tended to focus on the stability that remaining a part of Massachusetts offered, the larger population and economic potential of the two together, and the hopes (at least before the War of 1812) that Massachusetts would be a powerful ally in the event of a British invasion from New Brunswick.
Meanwhile, a small group of Mainers, especially in York County (west of Portland, and the location of the Portsmouth naval yard, in Kittery), favored joining New Hampshire, instead of becoming part of a new state. They had different aims from those wanting independence, but they shared the desire to be a part of a state that reflected their own political values and to which they were economically tied.
In both 1816 and 1819, the start of the Massachusetts legislative session was met with a flurry of petitions from Maine towns requesting the opportunity to vote on separation. Signed by thousands, these petitions revealed the rising popularity of the idea.
In these petitions, separatists provided numerous reasons why Maine should break off from Massachusetts. One, from the town of Hallowell, argued “the resources and extensive territory of Maine could be best called forth and improved by a local government.” They also claimed that education, so essential “to preserve the political virtue of our free and invaluable institutions,” could be better supported by a separate state of Maine.